Journal of the Chemical Society. Perkin transactions I p. 283 - 288 (1994)
Update date:2022-08-16
Topics:
Sakakura, Toshiyasu
Hara, Masayasu
Tanaka, Masato
α-Arylation of ketones is accomplished by the use of arenediazonium salts as aryl-cation equivalents.The reaction of silyl enol ethers with arenediazonium tetrafluoroborates proceeds in the presence of palladium(0) catalysts and tetraphenylborate anion to give α-aryl ketones in moderate yields.Alternatively, silyl enol ethers smoothly react with arenediazonium tetrafluoroborates in pyridine even without palladium catalysts and tetraphenylborate anion, affording arylated ketones in good yields.A mechanism involving addition of an aryl radical to a silyl enol ether is proposed for the latter process.
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